


Never Said It'd Be Easy

by phoenixwings



Category: Supernatural
Genre: Alternate Universe - High School, Alternate Universe - Human, Awkward Dates, Awkward Kissing, Bisexual Dean, Brief Pining, Charlie/Dean friendship, Comforting Dean, Coming Out, F/F, F/M, Fluff, Friendship focused, Growing Up, High School and beyond, Implied/Referenced Underage Drinking, M/M, Male-Female Friendship, Mentioned Dean/Original female character, Mentioned Dean/Original male character, Multi, POV Dean Winchester, Platonic Cuddling, Platonic Kissing, Sexual Identity, Weddings, mentioned Dean/Cassie, mentioned Dean/Lisa, mentioned past Dean/Jo, temporary break-up
Language: English
Status: Completed
Published: 2014-12-17
Updated: 2014-12-17
Packaged: 2018-03-01 20:39:54
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 7,122
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2786993
Author URL: https://archiveofourown.org/users/phoenixwings/pseuds/phoenixwings
Summary: <blockquote class="userstuff">
              <p><i>Charlie doesn’t hesitate when she sits down at their normal lunch table, just blurts out, “I have a crush and I need a favor.”</i><br/>High school, growing up, sexuality, relationships--it can all be pretty awkward, but it's better with friends who help you through.<br/>Or, three times Charlie and Dean kiss, and two times they don't.</p>
<p> </p>
<p><b>Note:</b> Charlie & Dean are never seriously romantically involved in this fic and the focus is on their friendship.</p>
            </blockquote>





	Never Said It'd Be Easy

**Author's Note:**

> Notes: I tagged this Charlie/Dean because as the summary suggests, they do kiss, but they are never seriously romantically involved and it's much more about both of them learning about themselves, navigating relationships, and friendship. Warning for implied underage drinking.
> 
> I can also be found on [Tumblr](http://burningphoenixwings.tumblr.com/).

Charlie doesn’t hesitate when she sits down at their normal lunch table, just blurts out, “I have a crush and I need a favor.”

“Oh,” Dean says, and steals one of her french fries. She swats at his hand. “Who? Is it Benny?”

 “What? No. No way.”

“Then who’s the guy?” Dean asks with a frown, because it’s not like Charlie to be so reluctant with information. Normally she doesn’t stop talking.

Charlie chews on her bottom lip a little and doesn’t even bother batting at Dean’s hand when he sneaks a second fry, so now he’s really curious and a bit weirded out because it’s like someone replaced his best friend. He wonders briefly is perhaps Charlie has been replaced by a robot, then shakes his head and thinks that Charlie’s been making him watch too much science fiction.

“It’s not a guy,” Charlie says finally, picking up her cafeteria burger with one hand and taking a large bite, looking at Dean only out of the corner of her eye.

“Oh,” Dean says again, pausing with Charlie’s french fry halfway to his mouth. This is news to him, but it’s not so surprising when he thinks about it. Charlie’s never paid attention to guys before. Dean just hadn’t realized she had been paying attention to girls. He's more surprised at how not surprised he is, honestly.

“Who’s the girl?” He asks.

“I don’t want to say yet. I need a favor.”

“Yeah, you mentioned,” Dean says. “What’s the favor?”

Charlie takes in a deep breath. “I need you to take me on a date.”

Okay, now Dean’s  _really_ confused. Charlie’s making no sense and he’s beginning to wonder if his friend sustained some sort of brain injury before school or if she has a fever. He’s even considering going back to the robot theory. Dean leans across the table and places the back of his hand on her forehead, but Charlie leans away from the touch.

“What are you doing?” She asks, looking puzzled, and Dean doesn’t understand why she’s the one who’s confused.

“Making sure you don’t have a fever,” He explains with a wave of his hand. “So. . . If you have a crush on a girl—and you won’t tell me who it is—why do you want me to take you on a date?”

“Because,” She explains, “I need to make sure this is a real crush before I decide to dance the Macarena out of the closet.”

“And me taking you out on a date is going to settle that how. . .?”

“You’re my best friend. If I’m ever gonna be attracted to a guy, it’d be you. Think of it as our movie moment. We go, have fun. If we don’t feel anything, then we’ve just hung out. We do that all the time anyway. But if not, then that’s the moment we look back on in fourteen years and realize when we liked each other and my crush on J—someone was just a passing phase. It’s the easiest way. You don't want to be thirty and realize you've secretly been pining for me all those years, do you?”

Dean thinks her logic is convoluted, but he’s not going to say so. Charlie looks focus, and Dean knows that expression. She could be determined when it came down to it. And really, they do hang out all the time anyway, so how terrible could a date be?

“Fine,” Dean concedes. Then he smirks. “So, her name starts with a J. Is it Jane Lewis? She’s pretty hot. Or maybe Jessi Baker. Or—”

“I'm not telling you."

“Fine,” Dean says, “I’m just gonna keep guessing.” Dean attempts to do so, but the bell signaling the end of lunch cuts him off at “Jenny Collins.”

“See you on Saturday!” Charlie calls over her shoulder.

 

* * *

 

The date is a disaster. Dean’s too mortified to beg for a ride from one of his parents for his first date ever, so he takes the bus to Charlie’s house. He can’t wait until he turns sixteen and gets his driver's license. His dad’s already promised Dean the Impala if Dean proves he can take care of it.

There’s a dollar theater within walking distance of her house, so they go there. It’s a bit run down and not nearly as good as the theater across town, but they’ve made do before. It’s different on a date, though. Dean doesn’t know exactly how far he’s suppose to take this in terms of being gentlemanly or whatever—he hesitates opening the door for Charlie and paying for the popcorn, not because he minds doing those things but because Charlie’s just always been around as his friend. They've been friends since first grade(not counting that one terrible year in fourth grade when Dean became friends with Gordon and was temporarily a jerk and Charlie stopped talking to him for eight months) and Dean's never thought of her as someone he would take on a date before.

Charlie’s clearly feeling just as awkward as he is, because she’s eerily quiet almost the entire time. The theater is playing Raiders of the Lost Ark, and there’s literally no one else in the theater, so normally they’d laugh and talk the entire way through it, pointing out fun facts they both know and joking about the characters together. Charlie barely even touches the popcorn. Dean's never felt uncomfortable around Charlie before, but he's quickly feeling more and more uneasy. Halfway through the movie Dean leans over and winds an arm around her shoulder, because he’s pretty sure that’s how a movie date is suppose to go, at least according to the movies he's seen, and they've committed to this. Charlie stiffens at first but then leans into it, and it’s still awkward but a little more normal. They’re friends, they touch all the time, it shouldn’t be weird—except now there’s all this pressure on every brush of skin against skin.

They don’t even talk as Dean walks Charlie home and up to her front door.

“So that was. . . fun,” Dean says, wincing at how obvious of a lie it is. Charlie doesn’t even bother replying to that, just stares at him.

“Um, so. . I guess I’ll see you later. . .” Dean trails off, turning to leave, but Charlie grabs his wrist.

“Wait,” She says, “We’ve been doing the whole date thing, right?”

“Yeah. . .” Dean replies, confused. She just looks at him like she’s willing him to get something without having to actually say it. Charlie cocks her head towards the door and narrows her eyes before Dean catches on.

“Oh,” He says, shuffling closer. He’s only kissed one person before—Jo, and was that ever a mistake, it was like kissing his sister—so he’s not exactly experienced, but kissing seems fairly intuitive. He bends down as Charlie reaches up and he brushes his lips against hers, light and just a feather-touch at first, before actually moving forward. It’s. . . fine. They don’t bump foreheads and neither of them have garlicky breath, so Dean figures they’re ahead of the curve already. It’s not exciting, exactly, but it feels pleasant enough. Dean doesn’t think either of them are very good at it, but it’s not horrible, and Charlie’s lips are plump and soft. It’s just fine, until Dean remembers that the lips he’s touching with his own are Charlie’s lips, and he pulls back suddenly because when he thinks about it kissing Charlie is just weird.

Charlie grimaces.

“So not a movie moment,” She says.

Dean shakes his head. “No way.”

“So, uh. . . Let’s pretend this never happened? And I think I’m definitely not into guys.”

“Yeah, let's do that. Don’t let me put you off my entire gender, though,” Dean says with a shy grin, and he’s rewarded when Charlie laughs. This is much better than whatever they were trying to do before.

“Sorry to break it to you, Winchester, but sadly I don’t think it’s just you.”

Dean huffs. “So now that we’re done the whole date thing and we’ve discovered we’re not soul mates, who's your crush?”

Charlie looks down at the porch. There’s a wayward nail sticking up from the wooden board and she kicks at it lightly with her converse.

“It’s, um, Jo,” Charlie mumbles.

“Jo?” Dean repeats, trying to not let his shock bleed over into his voice but pretty sure it happens anyway. He’s around Charlie and Jo all the time—he wonders how he managed to miss Charlie’s crush before. She’s more skilled at hiding her feelings than Dean would have guessed.

“Yeah,” Charlie confirms.

“You should ask her out,” Dean encourages, because it’s a little weird that his best friend would want to date his surrogate sister, but it also kind of pleases him. He hates most of the guys that Jo has talked about because they’re all dicks, and he knows Charlie would be better for her than any of the guys she’s glanced at so far.

“I don’t know if she’s even in to girls,” Charlie replies.

“I dunno,” He admits, “But you can ask. And even if she isn’t, Jo will be cool about it, you know that.”

“Yeah,” Charlie says again, but her voice still sounds distant. “Maybe.”

The porch light above them flickers three times, clearly being turned on and off from the inside, and Dean glances down at his watch. He needs to leave anyway to catch the bus and make it home by his curfew.

“Guess my mom wants me inside. Night,” Charlie says as she turns towards her door.

“See you Monday,” Dean says. Once Charlie’s inside, he walks quickly from her porch to the bus stop, eager to sleep off the strange evening. Normally, he’s not eager to go back to school Monday morning, but he’s ready to rush through the rest of this weekend so everything can go back to normal.

 

* * *

 

Charlie pouts at him.

“You didn’t wear your shirt,” She accuses with a glare. Dean glances down, because he really did thought he grabbed the right T-shirt this morning, but instead of his Browncoats t-shirt he’s wearing a plain grey tee with their school logo on it instead. It’s soft, worn and comfortable, so old that the screen-printed logo has started to crack.

“Sorry,” He says. “Grabbed the wrong shirt.” He’s not really that sorry, though, because the shirt he has on is really is comfortable and the T-shirt Charlie wanted him to wear is stiff and almost too small.

Charlie’s wearing an olive green tee with the Serenity printed on it, and holding up her Firefly DVD in one hand. When she plans a movie or TV day, she's insistent on them going all out. Once she even made themed food--not that Dean would ever complain about that, it had all been delicious.

“Fine, I’ll let you off the hook this time,” She sighs. “Next time there will be consequences.”

“Oh yeah? Like what?” Dean asks as he walks towards her kitchen to grab a soda out of the fridge. Mrs. Bradbury is sitting at the kitchen table listening to something through headphones, and she waves at him as he walks in. Dean returns the wave as he walks by.

The fridge is stocked so full of food that it takes Dean awhile to find the soda cans buried in the back. He has to stick most of his head in the fridge to reach the can of Pepsi he’s reaching for, so he misses Charlie’s no doubt sarcastic reply.

When he comes back Charlie already has the DVD in the player and they both settle on the couch, quoting most of the first episode together. Dean says Mal’s lines and Charlie takes the rest. At one point, Charlie pauses between episodes to take a bathroom break and when she comes back Dean decides to tell her his news.

“I asked Cassie Robinson out,” He says. He’s had a crush on Cassie for awhile, and Charlie’s known from the beginning.

“And?” She prompts.

“She said yes,” Dean says, looking down.

“Okay,” Charlie says, frowning a little. “So you asked the girl you have a crush on out and she agreed to go out with you. You don't look thrilled, though. I'm not getting the problem.”

Dean leans back against the couch, taking care to not look at Charlie dead-on when he asks his next question.

“Hey, so uh, is it true that girls sometimes kiss each other to practice?” Dean asks. It might make him a girl to admit(and Charlie would punch him if she heard him talk like that out loud), but he's actually pretty nervous about kissing a girl he barely knows. Kissing Jo and Charlie was weird, but at least he knew that even if he was the worst kisser in the world, it wouldn't have ruined his relationship with either one of them. Going out with Cassie makes him nervous.

“I don’t see what that has to do with any—” Charlie cuts off and narrows her eyes. “Uh-uh, Winchester. We did that once, remember? Back in January? Not something either of us wanted to repeat. Ringing any bells?”

“Yeah, but that’s when you told me to take you out on a date. This wouldn’t be like that, it’d just be, you know, practice. And it’s not like I have a crush on you or you have a crush on me, so. . . “

Charlie rolls her eyes, but Dean can tell the moment she gives in because her shoulders relax a little and there’s a smile tugging at the corner of her lips.

“Fine. But don’t you dare try to stick your tongue down my throat.”

Dean wrinkles his nose at the thought. That is not something he _ever_ plans to do with Charlie Bradbury. “Ew, no. Promise.”

Charlie smirks. “Well, what are you waiting for? Give it your best shot.”

They both move at the same time and actually do end up bumping foreheads this time. Charlie giggles and rubs at her head with her hand.

“That better not bruise. Try again,” She says, still laughing, so Dean does. Charlie’s wearing cherry lip balm and Dean can taste just a hint of it through their connected lips. He moves slowly, trying to figure out how to make it less sloppy and messy, and Dean can tell Charlie’s doing the same thing because she keeps angling her head differently or just barely parting her lips the tiniest bit. It’s not an amazing kiss by any means, Dean knows, but it’s actually better than the first time because there’s no date or intention of romance involved. It’s still a little weird that it’s Charlie, but Dean tries not to remember that part and just move mechanically. Eventually they got to a point where they’re moving together and Dean begins to relax. It’s a fairly long kiss, and Dean pulls away when he realizes he’s been holding his breath. He inhales deeply, glancing at Charlie. She leans back against the couch and smirks.

“So ready to wow Cassie with your new found kissing skills?” She asks, and Dean laughs because he knows it’s her way of easing things back into normal.

“I don’t know,” Dean replies, “Why don’t you ask Jo if you could test that technique out on her?” Charlie still hasn’t made a move on Jo, despite Dean’s frequent encouragement. At this rate he’s considering orchestrating some weird spin the bottle or seven minutes in heaven scenario, cliche as that is. Dean’s still not sure if Jo’s into girls, but he’s been watching their interactions more carefully now that he knows about Charlie’s crush, and the more he sees the more he thinks that Jo would be receptive.

Charlie responds to his teasing by tosses a piece of popcorn at him, so naturally Dean retaliates by throwing a Peanut M&M, but it backfires when Charlie manages to tilt her head at the perfect angle to catch it in her mouth. Dean goes for the popcorn next, launching a full-blown assault until the Bradbury’s faux leather couch is littered with white kernels.

* * *

 

Dean wakes up Saturday morning to someone pounding at the front door. He groans and throws on a shirt before taking the steps downstairs two at a time. If it’s a door-to-door salesman or even a girl scout with cookies trying to sell something, he swears. . .

It takes him some time to make it to the front door, but the knocking never lets up. Whoever it is, they're insistent. Dean curses as he opens the door, then immediately straightens up because it’s Charlie. Her face is tear-streaked and there’s a stray bit of mascara at the corner of her eye that makes it look like she never actually cleaned her face last night, just washed it with tears. Her normally groomed hair is frazzled and clearly hasn't been brushed and she’s wearing slippers instead of actual shoes.

“Charlie?”

She peers at the door into the empty house. His mom and dad left last night for a weekend couple’s retreat with stern instructions on not blowing all the money they left for meals on junk food, so it’s just him and Sam, who’s still asleep upstairs.

“Can I come in?” She asks in a wobbly voice. Dean nods and lets her inside, and she makes a beeline for the plush brown couch and sinks down on it. Dean sits on the opposite end and just waits for Charlie to speak.

“Jo broke up with me,” She says, finally looking at Dean. He shakes his head and mutters another swear under his breath. He'd been wondering if this was coming. After Charlie finally got up the courage to ask Jo out at the beginning of sophomore year, the two had been practically inseparable for the past two and a half years. While Dean had gone through his fair share of girls(and one or two guys, though no one really knew about that besides Charlie and Benny), Charlie and Jo had been together the entire time. After Christmas, though, Dean noticed that Jo started becoming more and more withdrawn and he saw the two of them fighting more often. They'd argue about the littlest things--which movie to see, whose car to take--but Dean thought the real issue was probably the fact they had both accepted their college offers and were going to different schools in the fall.

“Sorry,” Dean offers finally, though what he really wants to do is jump in the Impala, find Jo and drag her back, and knock some sense into both of them because the two of them are kind of perfect for each other and he knows how much Jo loves Charlie. Sometimes he can’t get her to shut up about the other girl, and Charlie’s just as bad.

Charlie stays silent for awhile, and eventually Dean clears his throat.

“Uh. . . Did Jo say why?” He asks, careful to keep his tone neutral.

Charlie shrugs. “She said there was no point in delaying the inevitable.”

Damn it, Jo. Now Dean’s more certain than ever that Jo’s breakup was a defensive mechanism because she was afraid. Jo’s going to the University of Kansas while Charlie’s headed off to MIT, and for two smart people they sure haven’t seemed to figure out that technological advances means that they could still communicate despite the distant. Dean doesn’t say anything because he knows that’s not what Charlie needs to hear at the moment.

“Your parents home?” Charlie asks, and Dean shakes his head. She sighs and pulls her legs up on the couch, wrapping her arms around them and letting her head rest on her knees. Dean can practically see the sorrow in her shoulders.

“I want to watch really awful science fiction movies and forget about this,” She declares finally. “And coffee.”

Dean offers her an easy grin. “You’ve got it,” He says, “Coffee and SyFy channel coming right up.”

He tosses the remote to her and goes to make the coffee, leaning against the counter as it brews. Once it’s done he brings two cups back into the living room and sets one on the coffee table in front of Charlie. She scoots over on the couch so she’s sitting closer to him and grabs the blanket that normally hangs over the back of the couch. She leans forward to reach for her coffee cup, but then she turns and looks at Dean, a strange expression in her eyes. Dean furrows his brow in confusion, but before he can ask what’s going on, Charlie reaches up and kisses him. She doesn’t waste time, either, bringing both of her hands up to rest on the back of his head and kissing with a ferocity Dean didn’t know she had. Dean’s too stunned at first to do anything but sit there, though it’s clear that Charlie has gained some skills since the last time they kissed almost three years ago at the end of freshman year. Of course, Dean has gained some skills and experience too, but it's the thought that Charlie has had lots of practice at this now--with Jo--that turns his mind back on and makes him jerk back with a yelp.

“What the hell, Charlie?” He asks in something that's not quite a shout, because Sam is still asleep upstairs, but close to one. Dean really wants to be furious, because Charlie just planted one on him even though he’s currently dating Lisa and she knows that, but Charlie looks so dejected when she finally looks back at him that Dean finds it difficult to keep a strong grip on his anger.

“Nope,” Charlie says, “Still not into guys.”

Dean sees tears start to well in the corner of her eyes and he sighs, knowing right there that he’ll never be able to be angry at her for this. He holds an arm open in invitation, and Charlie seems to get it, immediately curling up in his side and burying her face in his shoulder.

“You know,” Dean says once Charlie has mostly cried it out, “I bet if we called Ash he could hook us up with some beer for later, and my parents left money for food. We could order a pizza this evening, tell Benny to come over, watch bad movies, make a drinking game of it.”

“Ash is friends with Jo,” Charlie mumbles around dry sobs. Yeah, and so is Dean. He's not looking forward to navigating that situation come Monday morning, but right now Charlie's the one turning his shirt damp so he decides to deal with one thing at a time.

“So? We’re friends too. He’d do it.”

“Won’t Sam tell your parents when they get back?” Charlie asks, her breath more even now.

Dean shrugs. “I’ll offer to drive him over to Jess’ house. He’s always asking for a ride.”

Dean knew his brother had been crushing on Jess for months, and Sam was insufferable about denying it, but Dean didn’t think he’d turn down the free ride since Dean often refused when Sam asked for a ride unless their mom made him. In reality, Dean didn’t mind chauffeuring Sam around since it meant more time he got to spend in the Impala, but he didn’t like going over to the Moore’s house, because they lived beside the Miltons, and Dean just so happened to be nursing a huge crush on Castiel Milton. Dean hadn’t even told Charlie about it, because while he’d hooked up with two guys before, it had been just that—hook-ups. He’d only ever had actual relationships with girls(not that any of them lasted very long), and his family never knew the “Amber” he’d gone out with once had actually been an Alex. Making out or sleeping with a guy was easy to hide. It wouldn’t be as easy if he actually asked Castiel out, so he mostly tried to avoid the Milton’s house, and by extension the Moore’s, because every time Cas smiled at him his stomach did a girly flip, and the less he felt that the better.

“You don’t have plans with Lisa?” Charlie asks.

“No,” Dean lies. They hadn’t made any concrete plans, but they had talked about getting together over the weekend Friday at school. Still, he wasn’t going to let his best friend be upset alone, though he did feel a twinge of guilt in the bottom of his stomach. Lisa had made it clear that she was suspicious of Charlie, even though she knew Charlie only liked girls, and she did deserve better than Dean stringing her along. Lisa was adventurous and had a wicked sense of humor. She was gorgeous, and Dean liked her, but his feelings never went past that. They’d be going out for two months now, but in the past few weeks they’d be fighting almost constantly. He knew the break-up was coming. He shouldn't delay it any longer.

“I think I’m going to break up with her,” Dean admits.

“Oh,” Charlie said, taking the remote out of her hand. Dean thinks she looks a little too unsurprised by this statement, but due to the circumstances he decides to ignore it instead of pushing for an explanation.

“So is that a yes?” Dean asks. “Bad movies, scandalous underage drinking, pizza?”

“Okay,” Charlie agrees, giving him a tentative smile.

* * *

 

“There’s a ten percent chance of rain,” Anna says, looking up from her phone. Jo’s face drains of color and Dean throws Anna an exasperated look.

“Ten percent is nothing,” Dean tells Jo seriously. “Besides, I heard it’s good luck if it rains on your wedding day.”

Jo scowls at him.

“It’s gonna be fine,” He reassures, and Jo doesn’t say anything but nods and takes a deep breath.

“Ready to get into your dress?” Anna asks. Jo glances at the dress hanging over the door with a look of apprehension that would make more sense if it was cast towards a feral dog than a peach-colored dress.

“Think that’s your cue,” Jo says to Dean. “Time for you to go do your best man thing.”

Dean chuckles and gives her a hug before she has a chance to protest.

“Go get ‘em, Joanna Beth,” He says, and laughs when she swats at him.

The scene outside Charlie’s dressing room is less chaotic. He knocks on the door, and when Charlie opens it she’s fully dressed with her hair and make-up done—or so Dean assumes, since no one’s in a frenzy like they were in Jo’s room. Dean smiles at her in her dress. Charlie had debated forever whether to go for a dress or a suit, since she didn’t really prefer either, but she eventually settled on a dress since it was an outdoor summer wedding. Unlike Jo’s, Charlie’s dress is actually white, but it’s still only knee-length and pretty low on the frills. Her hair is done up and she can’t seem to keep a nervous smile off her face. Dean would never admit it out loud, but if he was pressed he’d have to say she looks radiant.

“Ready to tie the knot?” He asks. When Charlie smiles up at him, he’s glad for the thousandth time that Charlie and Jo finally got their act together. His friends are better together than apart. After breaking up senior year, Jo and Charlie reconciled during winter break during their freshman year of college. They’d started dating again that spring, and decided to get married after graduation before Charlie starts grad school.

And, of course, he was Charlie’s best man. There had been some discussion over that—Charlie and Jo decided that rather than sticking to just groomsmen or bridesmaids they’d just invite whoever they wanted to be in the wedding party, and they hadn’t been able to decide who’s side Dean should be on. Dean had crowed for a week over that, and Charlie(and Sam) said it made him insufferable to be around. Eventually, they decided that Dean would be with Charlie and Sam would be with Jo, since they both wanted Sam in the wedding as well and Jo knew Sam better than Charlie did.

“Yeah,” Charlie replies, “How do I look?” She twirls around and her dress billows up from the bottom.

Dean grins because he knows she’s not expecting a serious answer from him, so he adopts an exaggerated accent and says, “Why Mrs. Bradbury, you look positively dashing tonight.”

Charlie rolls her eyes. “That sounds almost seductive, Mr. Winchester. You are aware I am to wed another this very night, aren’t you?”

Dean acts scandalized. “I’m rather sorry to hear that, Mrs. Bradbury. For I am sure I would have found courting you to be an experience pleasing beyond all measure.”

Charlie cracks first, her lips splitting into a grin and she doubles over in laughter so hard she has to clutch her side. “We really need to work on your LARPing skills.”

“Hey,” Dean says, indignant, “I’m an excellent LARPer.” He glances at the clock on the wall and then back at Charlie, pleased to see that the rest of her nerves seemed to have been eased away by laughter.

"Okay, your accents then."

Dean scoffs.

“Seriously, you ready for this?” He asks.

Charlie nods. “This is the part where I hug you, so for once don’t hide the fact that you’re a big softie.”

Dean rolls his eyes but embraces Charlie just as tightly as she clings to him. “I hugged Jo too,” He admits.

“Softie,” Charlie mumbles into his dress shirt before pulling back. “Let’s get this party started, Winchester.”

The ceremony is simple, but everything is precisely planned. Dean knows that Jo and Charlie poured over every single detail before they decided on anything. He walks in with Charlie first, so he’s standing at the front of the ceremony area when the rest of the wedding party arrives. Sam walks down with a petite girl, one of Charlie’s friends from college, and Dean can’t help the snort he lets out at the size difference. Charlie subtly steps on his foot, and it’s lucky for Dean that she’s not wearing heels but instead has on a pair of simple sandals. He behaves after that.

Dean zones out a little once the officiant starts talking, instead casting encouraging smiles to both Charlie and Jo. It’s a little cooler than one would expect for a late July wedding, but the threatened rain never appears, and everything’s going smoothly.

Charlie and Jo exchange fairly traditional vows, their eyes staying glued to each other. Dean can tell that Charlie has tears in the corner of her eyes and though he’s loathed to admit it, he’s not far from that himself. Even Benny, who’s standing right beside him, looks affected. He spares a glance out at the audience and he’s pleased to see that he’s not the only one who’s a little misty-eyed.

Then, the officiant presents them as “Mrs. And Mrs. Harvelle-Bradbury” and tells both of them that they may kiss the bride. At the angle Dean’s standing he can see them clearly, and they seem reluctant to let go of each other as the kiss lingers. Dean knows that one or both of them will punch him for it later, but he figures it’s his duty as Charlie’s best man to let out a whistle when they still haven't broken apart after several seconds. Charlie pulls back, looking sheepish, and then the Imperial March—Charlie’s pick, because who else—starts playing as the signal the ceremony has ended.

 

Dean’s too busy stuffing his face with the grilled chicken and wild rice to really pick up on the conversation at first. He only lifts his head up when he hears Charlie say his name. The reception isn't very large, but it’s a loud bunch, and Dean has to strain to hear the other people at the wedding party’s table. They’re apparently discussing past romantic endeavors. Neither Charlie nor Jo have that many, except for their freshman year of college when they weren’t together, but apparently the few they did have contain some hilarious stories, because they're both cracking up.

“Here’s to the only boy I ever kissed,” Charlie says, raising a wine glass his way. Dean chuckles and lifts his own glass. He brings it to his lips and tries and fails to not pucker his mouth at the taste. He makes a mental note to find the beer once he’s finished with his meal.

“What?” Jo asks, turning to her wife.

“You didn’t know?” Charlie asks. “Dean was my first kiss.”

Uh-oh. Dean feels his cheeks starting to heat because he’s pretty sure he knows how the rest of this conversation is going to go. Jo’s fork clatters against the plate when she drops it and she turns a steady gaze towards Dean.

“No way,” Jo says, glancing back and forth between Dean and Charlie, “Dean was my first kiss too.”

“You never told me you kissed Jo,” Charlie says accusingly. “So, which of you did you kiss first?”

“Uh, it was Jo,” Dean mutters and rubs at the back of his neck. Just his luck that the first two girls he ever kissed were both his quasi-sisters. Sam, who up until that point had been deep into a conversation with Madison, one of Jo’s bridesmaids, breaks out into a barking laugh.

“Dude, you kissed your lesbian best friend and Jo?” Sam says. Dean groans.

“It was a long time ago! I was young and stupid.”

“How’s that different from now?” Benny teases in his slow drawl.

Dean grins. “Because now I’ve get skills in that department. Wanna hear about them?”

“No!” Sam, Jo, and Charlie all exclaim at the same time. Ha. Score one for Winchester. They move on to some other dull topic of conversation, so Dean decides to go searching for the beer to replace the wine he doesn’t like.

There’s a man with dark tufted hair standing by the drinks table, but Dean can’t place him, which is strange. He thought he knew almost everyone at the wedding. Dean reaches into a cooler for a beer and when he looks back up he’s met with blue eyes. He knows those eyes—he could never forget them. Dean feels his mouth go dry at the memory of his senior year crush. He hasn’t thought about Castiel in some time, even though his crush had lasted all throughout the last half of senior year and into the summer, fading only when Dean started college. He’d come out to his family and the few friends that didn’t know about his bisexuality during his sophomore year of college, and he’d forgotten there was a time he had ignored a crush because of that insecurity. Well, nothing like a second chance. He’d also forgotten that Castiel was Anna’s half-brother, so it made sense that Cas would become at least acquaintances with Jo just based on proximity.

Castiel looks even better four and a half years later. Dean may have gotten over his initial crush, but he’s beginning to think he’s already forming a new one. He knows what Castiel was like in high school—shy, a bit nerdy, but eager and kind. And focused. That was the thing about Castiel that had first caught Dean’s eyes. He’d notice that whatever Cas was doing, whether he was talking to someone or hunched over a math problem, Castiel gave whatever was right in front of him his full attention. The few times they’d interact, the intensity of Castiel’s gaze had almost set him back on his heels. Dean knows that people can change a lot in college, though. He had. He’d become more open, more accepting of himself. He wondered if Cas is different now too.

There’s no one else at the drinks table except for them—the music started awhile back and most of the guests have started dancing or mingling on the other side of the lawn.

“Hey,” Dean greets.

Castiel looks startled, but one corner of his mouth tugs up into something Dean thinks wants to be a smile when it grows up.

“Hello, Dean,” He says, and holds out a hand. “I’m Cas—”

“Castiel Milton, yeah,” Dean finishes before Cas fully introduces himself. “I remember you.”

That makes Castiel look even more surprised. “You do?”

“Course,” Dean replies, “Your family lived next door to the Moores, and Sam and Jess have been going out for years. I use to see you sometimes when I had to drive Sam around before he got his license.”

“Oh,” Cas replies, “I hadn’t realized.”

Dean doesn’t know what to say to that, so he pops the tab on the beer can and takes a big gulp. He’d just been boasting about his skills at the table and now he can barely keep up a conversation. Dean’s usually more suave, but this time he decides to be blunt.

“You around all summer? You graduated too, right?”

Cas nods. “I’m starting a graduate program for English in August at Stanford, but I’m around all summer. My older brother, Gabriel, insisted on another summer at home before I move to California.”

“Me too. I mean, I’m at home all summer. Not the grad school thing,” Dean says, wincing as he hears the words come out of his mouth. He stops and clears his throat before he asks, “So, Cas, would you want to-uh-get dinner sometime?”

Cas frowns at him, which isn’t the reaction that Dean hoped for.

“I’m sorry, I didn’t quite catch that,” Cas says.

Dean takes a deep breath and tries again. “Since we’re both at home this summer, would you want to get dinner with me sometime?”

Cas doesn’t frown this time, but he does squint up at Dean.

“I’m just curious, Dean,” Cas says, “I don’t quite understand why you want to be friends with me. We’ve barely talked now or in high school.”

“I don’t,” Dean replies too quickly, and then hangs his head and groans when he realizes how that sounds. “I mean, I don't want to be friends with you because I'm asking you out on a date. I, uh, had a crush on your in high school."

Well, might as well admit it now. Cas is moving to California in a month in a half, so if Cas is disturbed by his confession than they'll never have to see each other again.

For the third time in their increasingly awkward conversation, Cas looks surprised, but he recovers quickly and then he actually smiles.

“I think I’d like that,” Cas says, and Dean lets out a huge breath. He looks up and catches Charlie gazing at him with a strange expression across the lawn, and Dean realizes that he should probably get back to the rest of the wedding party.

“I should get back to Charlie,” Dean says.

Cas nods. “I’ll find you before I leave."

“Great,” Dean says, and then he promptly flees, casting a wink back over his shoulder, before he has a chance to mess it up by running his mouth some more.

 

* * *

 

Dean keeps glancing down at the phone he has balanced on his leg nervously. It doesn’t help that he keeps twitching his leg up and down before he can stop himself, and every time he has to scramble to catch his phone before it falls to the ground. He hates everything about flying, including airports. He hates how vulnerable he feels up in the sky, and he almost hates it even more when he’s picking people up from airports, because if they’re hurt up in the sky there’s nothing he can do about it. He’s unsettled, and his stomach is doing unpleasant gymnastics, and he had to take one of his precious vacation days to take off from the job he loves at the education non-profit to sit around in an airport and wait for Cas, who’s late.

Dean knows it’s not actually Cas’ fault he’s late, since it’s not like he can control the plane, but Dean’s irritation needs to be channel somewhere and it’s easier to be irritated at Cas because he’s not there yet.

Finally the airport boards flash up that Cas’ flight has arrived, and Dean lets out a sigh of relief. He doesn’t have to be afraid of his boyfriend’s body being wrecked in a cornfield somewhere. Dean keeps scanning the waiting area for a flash of black hair, but Cas seems to be taking his sweet time over in the baggage area. The airport is a complete circus—it’s so close to the holidays that it seems people just can’t stop flying to and fro. At the moment, Dean sort of hates them all on principle.

His irritation builds and builds while he keeps waiting, but as soon as he sees Cas’ blue eyes it slowly starts to eek out. Cas hurries over to him, and by the time he’s right in front of Dean, his well of irritation is completely empty.

“Dean,” Cas greets before he launches himself at Dean. Dean can’t help but to chuckle because he remembers how much it surprised him when they first started dating how affectionate Cas really is. Dean hadn’t thought him the type.

Dean squeezes Cas tightly and kisses up the other man’s jawline, his lips tracing over rough stubble. He’s missed the feel of this, the shape of Cas’ body in his arms and the heavy way Cas always says his name.

“I missed you,” Cas says, letting his head rest on Dean’s shoulder.

“Me too,” Dean says, and that seems to be it for Cas, because he raises his head from Dean’s shoulder and surges forward into a rough, passionate kiss. Dean can taste the peppermints that Cas is so fond of ildly chewing, and it’s not hard to taste because Cas is being liberal with his lips and tongue, sucking in Dean’s air supply and even though they’re still in public, Dean groans as Cas just keeps kissing him.

Eventually, Cas pulls back with wide eyes and moist lips. Cas lets his hands hang down by his side, so Dean takes one and threads his own fingers through it, giving it a squeeze as he catches his breath.

“I’ve been waiting to do that for months,” Cas says. Dean rubs a thumb over Cas’ knuckles.

“C’mon,” Dean says, “Let’s get out of here.” Cas beams up at him, and even though Dean really, really wants to get somewhere more private as soon as they can, the look Cas gives him is so focused and full that Dean can’t help but to kiss him again.

 

 


End file.
